Cimoxatone, MD-780515
西莫沙酮Chemical Name: 3-[4-[(3-Cyanophenyl)methoxy]phenyl]-5-(methoxymethyl)-2-oxazolidinone; 3-[[4-[5-(Methoxymethyl)-2-oxo-3-oxazolidinyl]phenoxy]methyl]benzonitrile
CAS No. 73815-11-9
项目整合开发状态: Biological Testing
项目研究机构: Delalande (Originator)
合成路线:The condensation of p-benzyloxyaniline (I) with 1-chloro-2-hydroxy-3-methoxypropane (II) in ethanol,followed by cyclization ot the resulting amino alcohol (III) with ethyl carbonate (A) in toluene in the presence of CH3ONa and debenzylation affords a phenolic 2-oxazolidinone (V),which is alkylated with m-cyanobenzyl bromide (VI) to give cimoxatone.
合成路线:A shorter synthetic pathway is through the condensation of the above chlorohydrin (II) with m-cyanobenzyloxyaniline (X),prepared by alkylation of p-nitrophenol (VIII) with m-cyanobenzyl bromide (VII) in the presence of KI and further reduction of the nitro group with Fe-NH4Cl,then cyclization with ethyl carbonate.Cimoxatone can also be obtained by opening glycidol (XI) with m-cyanobenzyloxyaniline (X) in ethanol under reflux,and cyclizing with ethyl carbonate (A) to obtain a 5-hydroxymethyl-2-oxazolidinone (XIII),which is methylated by CH3I under phase-transfer catalysis.
📌 参考资料/链接：
参考文献标题:Cimoxatone
文献作者:Ancher,J.F.
参考来源:Drugs Fut 1984,9(6),412
📄 详细内容
合成路线:The condensation of p-benzyloxyaniline (I) with 1-chloro-2-hydroxy-3-methoxypropane (II) in ethanol,followed by cyclization ot the resulting amino alcohol (III) with ethyl carbonate (A) in toluene in the presence of CH3ONa and debenzylation affords a phenolic 2-oxazolidinone (V),which is alkylated with m-cyanobenzyl bromide (VI) to give cimoxatone.
合成路线:A shorter synthetic pathway is through the condensation of the above chlorohydrin (II) with m-cyanobenzyloxyaniline (X),prepared by alkylation of p-nitrophenol (VIII) with m-cyanobenzyl bromide (VII) in the presence of KI and further reduction of the nitro group with Fe-NH4Cl,then cyclization with ethyl carbonate.Cimoxatone can also be obtained by opening glycidol (XI) with m-cyanobenzyloxyaniline (X) in ethanol under reflux,and cyclizing with ethyl carbonate (A) to obtain a 5-hydroxymethyl-2-oxazolidinone (XIII),which is methylated by CH3I under phase-transfer catalysis.
参考文献标题:Nouvelles oxazolidinones,oxazolidinethiones et pyrrilidinones,leur proc閐?de pr閜aration et leur application en th閞apeutique
文献作者:Ancher,J.F.; Bourgery,G.; Dostert,P.; Douzon,C.; Guerret,P.; Lacour,A.; Laglois,M.
参考来源:FR 2428032; JP 55051064; JP 56167666
产品链接: CAS No. 73815-11-9››